The objective of the proposed research is the enantioselective total synthesis of cornmunesin A. This compound belongs to the indole alkaloid family of natural products and has demonstrated promising anticancer activity through preliminary biological evaluation. The initial goal of this research is to develop a non-racemic synthesis for the azepinoindole subunit of communesin A that bears a close resemblance to another natural product aurantioclavine. Through manipulations to this key intermediate, two different substrates for a [3,3] sigmatropic rearrangement will be constructed. Substrate-specific rearrangement reactions utilizing a modified Carroll or modified Claisen strategy will provide compounds bearing the requisite adjacent quaternary carbons, stereoselectively. Further manipulations to the products from the rearrangement will provide a common intermediate which will possess three rings, two adjacent quaternary stereocenters, and the necessary functional handles required for completion of the natural product. Formation of the two aminal linkages through a sequential condensation approach and a late-stage epoxidation will afford non-racemic communesin A. Development of this synthesis will advance the techniques available for the construction of vicinal quaternary stereocenters and will provide a foundation for the chemistry necessary to manipulate this class of natural products in an effort to successfully probe biological activity. [unreadable] [unreadable]